CA2247167C - 2-hetaroylcyclohexane-1,3-diones - Google Patents

2-hetaroylcyclohexane-1,3-diones Download PDF

Info

Publication number: CA2247167C
Authority: CA; Canada
Prior art keywords: alkoxy; alkyl; halogen; hydrogen; cyano
Prior art date: 1996-02-24
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA002247167A

Other languages

English (en)

French (fr)

Other versions

CA2247167A1 (en

Inventor

Martina Otten

Wolfgang Von Deyn

Stefan Engel

Regina Luise Hill

Uwe Kardorff

Marcus Vossen

Peter Plath

Helmut Walter

Karl-Otto Westphalen

Ulf Misslitz

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1996-02-24

Filing date

1997-02-20

Publication date

2005-07-12

1996-02-24 Priority claimed from DE19607105A external-priority patent/DE19607105A1/de

1996-03-29 Priority claimed from DE1996112687 external-priority patent/DE19612687A1/de

1997-02-20 Application filed by BASF SE filed Critical BASF SE

1997-08-28 Publication of CA2247167A1 publication Critical patent/CA2247167A1/en

2005-07-12 Application granted granted Critical

2005-07-12 Publication of CA2247167C publication Critical patent/CA2247167C/en

2017-02-20 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 64
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 56
239000001257 hydrogen Substances 0.000 claims abstract description 55
229910052736 halogen Inorganic materials 0.000 claims abstract description 49
150000002367 halogens Chemical class 0.000 claims abstract description 49
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 41
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 40
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 30
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 28
125000005843 halogen group Chemical group 0.000 claims abstract description 16
125000001424 substituent group Chemical group 0.000 claims abstract description 11
229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
239000001301 oxygen Substances 0.000 claims abstract description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
238000004519 manufacturing process Methods 0.000 claims abstract 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2084
239000000460 chlorine Substances 0.000 claims description 202
-1 tetrahydropyran-3-yl Chemical group 0.000 claims description 80
150000001875 compounds Chemical class 0.000 claims description 42
239000000203 mixture Substances 0.000 claims description 32
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 30
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 25
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 25
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 16
230000002363 herbicidal effect Effects 0.000 claims description 10
238000000034 method Methods 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 8
239000003054 catalyst Substances 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical group O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 3
239000000126 substance Substances 0.000 claims description 3
125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 2
230000010933 acylation Effects 0.000 claims description 2
238000005917 acylation reaction Methods 0.000 claims description 2
239000000654 additive Substances 0.000 claims description 2
125000002837 carbocyclic group Chemical group 0.000 claims description 2
UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims description 2
230000008635 plant growth Effects 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 28
150000002431 hydrogen Chemical class 0.000 abstract description 23
241000196324 Embryophyta Species 0.000 abstract description 16
239000003795 chemical substances by application Substances 0.000 abstract description 3
239000005864 Sulphur Chemical group 0.000 abstract 1
125000006193 alkinyl group Chemical group 0.000 abstract 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 45
239000002904 solvent Substances 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 18
239000002585 base Substances 0.000 description 17
239000000047 product Substances 0.000 description 17
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
239000000243 solution Substances 0.000 description 13
239000003921 oil Substances 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
239000006185 dispersion Substances 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 7
238000005160 1H NMR spectroscopy Methods 0.000 description 6
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
238000005481 NMR spectroscopy Methods 0.000 description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000013543 active substance Substances 0.000 description 5
235000010233 benzoic acid Nutrition 0.000 description 5
229910002091 carbon monoxide Inorganic materials 0.000 description 5
239000004359 castor oil Substances 0.000 description 5
235000019438 castor oil Nutrition 0.000 description 5
239000012141 concentrate Substances 0.000 description 5
244000038559 crop plants Species 0.000 description 5
239000000839 emulsion Substances 0.000 description 5
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 5
230000012010 growth Effects 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 5
239000002184 metal Substances 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
238000011282 treatment Methods 0.000 description 5
101150041968 CDC13 gene Proteins 0.000 description 4
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
150000001559 benzoic acids Chemical class 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
238000000605 extraction Methods 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
239000011707 mineral Substances 0.000 description 4
235000010755 mineral Nutrition 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
150000003003 phosphines Chemical group 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
229910052723 transition metal Inorganic materials 0.000 description 4
150000003672 ureas Chemical class 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
240000008042 Zea mays Species 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
229910000288 alkali metal carbonate Chemical group 0.000 description 3
150000008041 alkali metal carbonates Chemical group 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
235000013877 carbamide Nutrition 0.000 description 3
238000006473 carboxylation reaction Methods 0.000 description 3
239000000969 carrier Substances 0.000 description 3
230000006378 damage Effects 0.000 description 3
238000010410 dusting Methods 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
239000008187 granular material Substances 0.000 description 3
239000004009 herbicide Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000002480 mineral oil Substances 0.000 description 3
235000010446 mineral oil Nutrition 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000006072 paste Substances 0.000 description 3
229910000073 phosphorus hydride Inorganic materials 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
230000008707 rearrangement Effects 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
238000001291 vacuum drying Methods 0.000 description 3
YOLVBJUSDXESQT-LSLKUGRBSA-N (2S)-2-amino-N-(1-diphenoxyphosphorylethyl)propanamide Chemical compound C=1C=CC=CC=1OP(=O)(C(C)NC(=O)[C@@H](N)C)OC1=CC=CC=C1 YOLVBJUSDXESQT-LSLKUGRBSA-N 0.000 description 2
125000006059 1,1-dimethyl-2-butenyl group Chemical group 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
125000006028 1-methyl-2-butenyl group Chemical group 0.000 description 2
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 2
WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 2
MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 2
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
240000002791 Brassica napus Species 0.000 description 2
235000011293 Brassica napus Nutrition 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
244000068988 Glycine max Species 0.000 description 2
244000299507 Gossypium hirsutum Species 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
239000002841 Lewis acid Substances 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
240000007594 Oryza sativa Species 0.000 description 2
235000007164 Oryza sativa Nutrition 0.000 description 2
229910002666 PdCl2 Inorganic materials 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
241001506137 Rapa Species 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
235000002594 Solanum nigrum Nutrition 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
241000209140 Triticum Species 0.000 description 2
235000021307 Triticum Nutrition 0.000 description 2
244000098338 Triticum aestivum Species 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000001464 adherent effect Effects 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
150000003973 alkyl amines Chemical group 0.000 description 2
150000008055 alkyl aryl sulfonates Chemical group 0.000 description 2
150000005215 alkyl ethers Chemical class 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
150000001555 benzenes Chemical class 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
159000000007 calcium salts Chemical class 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
229910017052 cobalt Inorganic materials 0.000 description 2
239000010941 cobalt Substances 0.000 description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical compound O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 description 2
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
UWNROJGZIJOEKB-UHFFFAOYSA-N ethyl 2-methyl-3-(2-methylsulfonylsulfanylethoxy)benzoate Chemical compound CCOC(=O)C1=CC=CC(OCCSS(C)(=O)=O)=C1C UWNROJGZIJOEKB-UHFFFAOYSA-N 0.000 description 2
SDVVYXIRTIFLNR-UHFFFAOYSA-N ethyl 3-(2-bromoethoxy)-2-methylbenzoate Chemical compound CCOC(=O)C1=CC=CC(OCCBr)=C1C SDVVYXIRTIFLNR-UHFFFAOYSA-N 0.000 description 2
QPFMYHYVFTWBNS-UHFFFAOYSA-N ethyl 8-methyl-2,3-dihydro-1,4-benzoxathiine-7-carboxylate Chemical compound S1CCOC2=C(C)C(C(=O)OCC)=CC=C21 QPFMYHYVFTWBNS-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
230000035784 germination Effects 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
150000007517 lewis acids Chemical class 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
150000002790 naphthalenes Chemical class 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
SMOOPNYQNKPFGT-UHFFFAOYSA-M potassium;methyl-oxido-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound [K+].CS([O-])(=O)=S SMOOPNYQNKPFGT-UHFFFAOYSA-M 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000000376 reactant Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229910052703 rhodium Inorganic materials 0.000 description 2
239000010948 rhodium Substances 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
241000894007 species Species 0.000 description 2
239000007921 spray Substances 0.000 description 2
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125000004122 cyclic group Chemical group 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
150000004891 diazines Chemical class 0.000 description 1
239000002283 diesel fuel Substances 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
BADXJIPKFRBFOT-UHFFFAOYSA-N dimedone Chemical compound CC1(C)CC(=O)CC(=O)C1 BADXJIPKFRBFOT-UHFFFAOYSA-N 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
239000010459 dolomite Substances 0.000 description 1
229910000514 dolomite Inorganic materials 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
229940052303 ethers for general anesthesia Drugs 0.000 description 1
WWTLEVOTRVPTOD-UHFFFAOYSA-N ethyl 3-hydroxy-2-methylbenzoate Chemical compound CCOC(=O)C1=CC=CC(O)=C1C WWTLEVOTRVPTOD-UHFFFAOYSA-N 0.000 description 1
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
235000004426 flaxseed Nutrition 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
238000010353 genetic engineering Methods 0.000 description 1
235000002532 grape seed extract Nutrition 0.000 description 1
238000000227 grinding Methods 0.000 description 1
150000003977 halocarboxylic acids Chemical class 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000003864 humus Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229910000043 hydrogen iodide Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
150000002460 imidazoles Chemical class 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000003446 ligand Substances 0.000 description 1
239000004571 lime Substances 0.000 description 1
239000006028 limestone Substances 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
235000005739 manihot Nutrition 0.000 description 1
235000012054 meals Nutrition 0.000 description 1
VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
231100001184 nonphytotoxic Toxicity 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
235000016709 nutrition Nutrition 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000004866 oxadiazoles Chemical class 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
150000008048 phenylpyrazoles Chemical class 0.000 description 1
230000003032 phytopathogenic effect Effects 0.000 description 1
SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
239000001739 pinus spp. Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
208000003383 pontocerebellar hypoplasia type 3 Diseases 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003217 pyrazoles Chemical class 0.000 description 1
150000004892 pyridazines Chemical class 0.000 description 1
LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
235000013526 red clover Nutrition 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
210000000614 rib Anatomy 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
239000004576 sand Substances 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
125000005624 silicic acid group Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
239000002689 soil Substances 0.000 description 1
238000009331 sowing Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000005507 spraying Methods 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
150000003566 thiocarboxylic acids Chemical class 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
239000004562 water dispersible granule Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/32—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms six-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/08—Six-membered rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (AREA)
General Health & Medical Sciences (AREA)
Pest Control & Pesticides (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)

CA002247167A 1996-02-24 1997-02-20 2-hetaroylcyclohexane-1,3-diones Expired - Fee Related CA2247167C (en)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
DE19607105.4		1996-02-24
DE19607105A DE19607105A1 (de)	1996-02-24	1996-02-24	2-Hetaroylcyclohexan-1,3-dione
DE1996112687 DE19612687A1 (de)	1996-03-29	1996-03-29	2-Hetaroylcyclohexan-1,3-dione
DE19612687.8		1996-03-29
PCT/EP1997/000802 WO1997030986A1 (de)	1996-02-24	1997-02-20	2-hetaroylcyclohexan-1,3-dione

Publications (2)

Publication Number	Publication Date
CA2247167A1 CA2247167A1 (en)	1997-08-28
CA2247167C true CA2247167C (en)	2005-07-12

Family

ID=26023221

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002247167A Expired - Fee Related CA2247167C (en)	1996-02-24	1997-02-20	2-hetaroylcyclohexane-1,3-diones

Country Status (19)

Country	Link
US (1)	US6013607A (ja)
EP (1)	EP0888334B1 (ja)
JP (1)	JP2000505449A (ja)
KR (1)	KR19990087187A (ja)
CN (1)	CN1096458C (ja)
AR (1)	AR005956A1 (ja)
AT (1)	ATE221526T1 (ja)
AU (1)	AU728500B2 (ja)
BG (1)	BG64005B1 (ja)
BR (1)	BR9707721A (ja)
CA (1)	CA2247167C (ja)
CZ (1)	CZ268198A3 (ja)
DE (1)	DE59707863D1 (ja)
EA (1)	EA001930B1 (ja)
IL (1)	IL125550A (ja)
NZ (1)	NZ331123A (ja)
PL (1)	PL328505A1 (ja)
SK (1)	SK282671B6 (ja)
WO (1)	WO1997030986A1 (ja)

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US6440899B1 (en)	1998-04-30	2002-08-27	Basf Aktiengesellschaft	Cyclohexenonedioxothiochromanoyl derivatives
CA2355125A1 (en) *	1998-12-15	2000-06-22	Basf Aktiengesellschaft	Thiochromanoylcyclohexenone derivatives
AR023255A1 (es) *	1999-05-13	2002-09-04	Idemitsu Kosan Co	Compuestos azoles y composiciones herbicidas que los contienen
WO2001074802A1 (en) *	2000-04-04	2001-10-11	Idemitsu Kosan Co., Ltd.	Fused-benzoyl derivatives and herbicide compositions containing the same
WO2002032373A2 (en) *	2000-10-19	2002-04-25	Merck & Co., Inc.	Estrogen receptor modulators
US6750213B2 (en)	2000-10-19	2004-06-15	Merck & Co., Inc.	Estrogen receptor modulators
DK1501819T3 (da)	2002-04-24	2011-01-10	Merck Sharp & Dohme	Østrogenreceptormodulatorer
WO2011117195A1 (en)	2010-03-23	2011-09-29	Basf Se	Substituted pyridines having herbicidal action
AR081526A1 (es)	2010-03-23	2012-10-03	Basf Se	Piridazinas sustituidas que tienen accion herbicida
CN102822179A (zh)	2010-03-23	2012-12-12	巴斯夫欧洲公司	具有除草作用的吡嗪并噻嗪
CA2791612A1 (en)	2010-03-23	2011-09-29	Basf Se	Pyridothiazines having herbicidal action
WO2011117210A1 (en)	2010-03-23	2011-09-29	Basf Se	Substituted pyridines having herbicidal action
CN102858780A (zh)	2010-03-23	2013-01-02	巴斯夫欧洲公司	具有除草作用的取代哒嗪
JP2014501742A (ja)	2010-12-23	2014-01-23	ビーエーエスエフソシエタス・ヨーロピア	除草活性を有する置換ピリジン
WO2012168241A1 (en)	2011-06-09	2012-12-13	Basf Se	Substituted pyrazines having herbicidal activity
CN103596959A (zh)	2011-06-09	2014-02-19	巴斯夫欧洲公司	具有除草活性的取代吡啶类
CA2853340A1 (en)	2011-11-16	2013-05-23	Basf Se	Substituted 1,2,5-oxadiazole compounds and their use as herbicides ii
BR112014026823A2 (pt)	2012-04-27	2017-06-27	Basf Se	compostos de n-(tetrazol-5-il) e n-(triazol-5-il)arilcarboxamida substituída e seu uso como herbicidas.
BR112014029531A2 (pt)	2012-06-01	2017-06-27	Basf Se	composto de piridina, composição e método para controlar vegetação indesejada
JP2014105156A (ja) *	2012-11-22	2014-06-09	Sumitomo Seika Chem Co Ltd	環状ジスルホン化合物の製造方法
WO2014184019A1 (en)	2013-05-15	2014-11-20	Basf Se	N-(1,2,5-oxadiazol-3-yl)carboxamide compounds and their use as herbicides
CN105246900A (zh)	2013-05-24	2016-01-13	巴斯夫欧洲公司	具有除草活性的取代吡啶化合物

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Publication number	Priority date	Publication date	Assignee	Title
US4249937A (en) *	1977-05-23	1981-02-10	Nippon Soda Company, Ltd.	Cyclohexane derivatives
US4780127A (en) *	1982-03-25	1988-10-25	Stauffer Chemical Company	Certain 2-(substituted benzoyl)-1,3-cyclohexanediones and their use as herbicides
IL77349A (en) *	1984-12-20	1990-07-12	Stauffer Chemical Co	2-(2'-nitrobenzoyl)-1,3-cyclohexanediones,their preparation and their use as herbicides
EP0243313B1 (de) *	1986-04-24	1990-05-16	Ciba-Geigy Ag	Acyl-cyclohexandione und deren Oximäther mit herbizider und das Pflanzenwachstum regulierender Wirkung
CA1340284C (en) *	1987-03-19	1998-12-22	Zeneca Inc.	Herbicidal substituted cyclic diones
JPH04247052A (ja) *	1991-01-31	1992-09-03	Nippon Soda Co Ltd	ビシクロ〔４，１，０〕ヘプタン−２，４−ジオン誘導体、その製造法
WO1994004524A1 (fr) *	1992-08-18	1994-03-03	Idemitsu Kosan Co., Ltd.	Derive de cyclohexanedione
AU5118693A (en) *	1992-10-15	1994-05-09	Idemitsu Kosan Co. Ltd	Cyclohexanedione derivative
JPH08245618A (ja) *	1995-03-08	1996-09-24	Nippon Soda Co Ltd	置換ビシクロヘプタンジオン誘導体および除草剤

1997
- 1997-02-20 AT AT97906099T patent/ATE221526T1/de not_active IP Right Cessation
- 1997-02-20 CN CN97192484A patent/CN1096458C/zh not_active Expired - Fee Related
- 1997-02-20 AU AU20918/97A patent/AU728500B2/en not_active Ceased
- 1997-02-20 CA CA002247167A patent/CA2247167C/en not_active Expired - Fee Related
- 1997-02-20 BR BR9707721-6A patent/BR9707721A/pt active Search and Examination
- 1997-02-20 JP JP9529796A patent/JP2000505449A/ja not_active Withdrawn
- 1997-02-20 EA EA199800759A patent/EA001930B1/ru not_active IP Right Cessation
- 1997-02-20 KR KR1019980706582A patent/KR19990087187A/ko not_active Abandoned
- 1997-02-20 CZ CZ982681A patent/CZ268198A3/cs unknown
- 1997-02-20 NZ NZ331123A patent/NZ331123A/xx unknown
- 1997-02-20 US US09/125,378 patent/US6013607A/en not_active Expired - Fee Related
- 1997-02-20 SK SK1034-98A patent/SK282671B6/sk unknown
- 1997-02-20 DE DE59707863T patent/DE59707863D1/de not_active Expired - Lifetime
- 1997-02-20 WO PCT/EP1997/000802 patent/WO1997030986A1/de not_active Ceased
- 1997-02-20 PL PL97328505A patent/PL328505A1/xx unknown
- 1997-02-20 IL IL12555097A patent/IL125550A/en not_active IP Right Cessation
- 1997-02-20 EP EP97906099A patent/EP0888334B1/de not_active Expired - Lifetime
- 1997-02-21 AR ARP970100712A patent/AR005956A1/es not_active Application Discontinuation
1998
- 1998-08-19 BG BG102701A patent/BG64005B1/bg unknown

Also Published As

Publication number	Publication date
US6013607A (en)	2000-01-11
BG102701A (en)	1999-04-30
CZ268198A3 (cs)	1999-02-17
BR9707721A (pt)	2005-06-07
ATE221526T1 (de)	2002-08-15
BG64005B1 (bg)	2003-09-30
SK103498A3 (en)	1999-03-12
CN1211979A (zh)	1999-03-24
EP0888334B1 (de)	2002-07-31
WO1997030986A1 (de)	1997-08-28
AU2091897A (en)	1997-09-10
KR19990087187A (ko)	1999-12-15
IL125550A0 (en)	1999-03-12
PL328505A1 (en)	1999-02-01
CN1096458C (zh)	2002-12-18
NZ331123A (en)	2000-03-27
IL125550A (en)	2001-11-25
AU728500B2 (en)	2001-01-11
AR005956A1 (es)	1999-07-21
EA001930B1 (ru)	2001-10-22
DE59707863D1 (de)	2002-09-26
JP2000505449A (ja)	2000-05-09
CA2247167A1 (en)	1997-08-28
EP0888334A1 (de)	1999-01-07
SK282671B6 (sk)	2002-11-06
EA199800759A1 (ru)	1999-04-29

Legal Events

Date	Code	Title	Description
2002-02-12	EEER	Examination request
2007-02-20	MKLA	Lapsed

Publication	Publication Date	Title
CA2247167C (en)	2005-07-12	2-hetaroylcyclohexane-1,3-diones
AU717015B2 (en)	2000-03-16	Benzoyl derivatives
US5744425A (en)	1998-04-28	Saccharin derivatives
US5925767A (en)	1999-07-20	Pyrazole-4-yl-hetaroyl derivatives as herbicides
US5863864A (en)	1999-01-26	Preparation of saccharincarboxylic acids and -carboxylic acid esters
US6291682B1 (en)	2001-09-18	Pyrazol-4-ylbenzoyl derivatives and their use as herbicides
US5716906A (en)	1998-02-10	Saccharin derivatives
US5716905A (en)	1998-02-10	Saccharin derivatives
US5723415A (en)	1998-03-03	5-hydroxypyrazol-4-ylcarbonyl-substituted saccharin derivatives
WO1997019071A1 (de)	1997-05-29	2-cyano-1,3-dion derivate, deren herstellung und deren verwendung als herbizide
CA2283491A1 (en)	1998-09-17	Saccharine-5-carbonyl-cyclohexane-1,3,5-trione derivatives, their preparation and their use as herbicides
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